US2743246A - Method of polycondensation of alkylene-, alkylidene-and aralkylidene-bishalogen substituted carboxylic acid amides - Google Patents

Method of polycondensation of alkylene-, alkylidene-and aralkylidene-bishalogen substituted carboxylic acid amides Download PDF

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Publication number
US2743246A
US2743246A US299734A US29973452A US2743246A US 2743246 A US2743246 A US 2743246A US 299734 A US299734 A US 299734A US 29973452 A US29973452 A US 29973452A US 2743246 A US2743246 A US 2743246A
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United States
Prior art keywords
polycondensation
bishalogen
aralkylidene
alkylidene
alkylene
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Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
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US299734A
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English (en)
Inventor
Lotz Rudolf
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Glanzstoff AG
Vereinigte Glanzstoff Fabriken AG
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Glanzstoff AG
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/02—Polyamines
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B03—SEPARATION OF SOLID MATERIALS USING LIQUIDS OR USING PNEUMATIC TABLES OR JIGS; MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
    • B03B—SEPARATING SOLID MATERIALS USING LIQUIDS OR USING PNEUMATIC TABLES OR JIGS
    • B03B13/00—Control arrangements specially adapted for wet-separating apparatus or for dressing plant, using physical effects
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B03—SEPARATION OF SOLID MATERIALS USING LIQUIDS OR USING PNEUMATIC TABLES OR JIGS; MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
    • B03D—FLOTATION; DIFFERENTIAL SEDIMENTATION
    • B03D1/00—Flotation
    • B03D1/02—Froth-flotation processes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
    • C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/02—Polyamines
    • C08G73/028—Polyamidoamines

Definitions

  • This compound has a melting point of 240 C. If this monoamine is treated in a vacuum of 0.5 mm. Hg, and at a temperature of 115 C. in a current of nitrogen, there is obtained while HCl is split off quantitatively in the distillation vessel a light colored polycondensation product which is useful for the production of plastic masses.
  • the diamine thus obtained which has a melting point of 140 C., can also be condensed with adipic acid and yields a polycondensate having a linear structure. It is excellently suited for the production of plastic masses.
  • This monoamine has a melting-point (if-124W: C.
  • This compound is melted while introducing nitrogen at normal pressure, and is heated in a vacuum of 2 mm. Hg to about -l90 C., which temperature is maintained for 3 hours. In the course of condensation hydrochloric acid is split off. The lightly colored condensation product remaining in the distillation vessel when the reaction is completed, lends itself to the production of plastic masses.
  • Example 11 200 grams of methylene-bis-chloropropionic acid amide and 1000 cc. of liquid ammonia are heated in the autoclave for up to 20 hours at a pressure of up to about 20 atm. and a temperature of about 60 C. A homogeneous liquid is formed. Upon evaporation of excessive ammonia and after removal of inorganic reaction products, a solid product is obtained which has a melting point of 140 C. and is the diamine of the methylene-bis-chloropropionic acid amide.
  • Example 111 100 grams of ethylidene-bis-chloropropionic acid amide are treated with 1000 cc. of liquid ammonia for up to 20 hours, at room temperature, in the autoclave, at a pressure of about 8-10 atm. A homogeneous liquid is formed which on evaporation of the excess of ammonia, leaves behind a semi-solid mass. From this mass a solid product is isolated which melts at l90 C. It is the monoamine of the ethylidene-bis-chloropropionic acid amide of the following formula:
  • I claim: 1. The process of preparing a light colored condensation product of a monoamine of the general formula wherein Hal means halogen, n is an integer from 1 to 6 and R is a member of the group consisting of hydrogen and methyl, which comprises reacting a bis-amide of the general formula Hal.(CH;

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyamides (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US299734A 1951-07-26 1952-07-18 Method of polycondensation of alkylene-, alkylidene-and aralkylidene-bishalogen substituted carboxylic acid amides Expired - Lifetime US2743246A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2743246X 1951-07-26
DE317129X 1951-07-26

Publications (1)

Publication Number Publication Date
US2743246A true US2743246A (en) 1956-04-24

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US299734A Expired - Lifetime US2743246A (en) 1951-07-26 1952-07-18 Method of polycondensation of alkylene-, alkylidene-and aralkylidene-bishalogen substituted carboxylic acid amides

Country Status (4)

Country Link
US (1) US2743246A (enrdf_load_stackoverflow)
BE (1) BE513053A (enrdf_load_stackoverflow)
GB (1) GB734287A (enrdf_load_stackoverflow)
NL (1) NL82429C (enrdf_load_stackoverflow)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3335181A (en) * 1964-04-17 1967-08-08 Hoffmann La Roche Ammonolysis of 2-halo-2'-benzoyl-4'-nitroacetanilides
US6365706B1 (en) 2000-06-21 2002-04-02 Mississippi Chemical Corporation Process for production of polyasparagine and the high nitrogen content polymer formed thereby

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2109929A (en) * 1937-03-15 1938-03-01 Du Pont Preparation of amino acids
FR882106A (fr) * 1939-05-11 1943-05-18 Ig Farbenindustrie Ag Diamides di-béta-chloropropioniques, diamides diacryliques, produits de polymérisation de celles-ci et procédé de préparation de ces corps
US2338177A (en) * 1938-10-14 1944-01-04 Chem Ind Basel Condensation product and process of making same

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2109929A (en) * 1937-03-15 1938-03-01 Du Pont Preparation of amino acids
US2338177A (en) * 1938-10-14 1944-01-04 Chem Ind Basel Condensation product and process of making same
FR882106A (fr) * 1939-05-11 1943-05-18 Ig Farbenindustrie Ag Diamides di-béta-chloropropioniques, diamides diacryliques, produits de polymérisation de celles-ci et procédé de préparation de ces corps

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3335181A (en) * 1964-04-17 1967-08-08 Hoffmann La Roche Ammonolysis of 2-halo-2'-benzoyl-4'-nitroacetanilides
US6365706B1 (en) 2000-06-21 2002-04-02 Mississippi Chemical Corporation Process for production of polyasparagine and the high nitrogen content polymer formed thereby
US6562941B2 (en) 2000-06-21 2003-05-13 Mississippi Chemical Corporation Process for production of polyasparagine and the high nitrogen content polymer formed thereby

Also Published As

Publication number Publication date
NL82429C (enrdf_load_stackoverflow)
GB734287A (en) 1955-07-27
BE513053A (enrdf_load_stackoverflow)

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